HCID 69027200, compound → HCID 17985220, compound

HRID 1433039Notes

Reaction equation

HRID 1433039 reaction equation
Cl.C(OC([N:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[C:21]([NH2:27])[CH:20]=2)[C:14](=[O:28])[CH2:13]1)=O)C1C=CC=CC=1>CO.C(Cl)Cl.[Pd]>[NH2:27][C:21]1[CH:20]=[C:19]([CH2:18][N:15]2[CH2:16][CH2:17][NH:12][CH2:13][C:14]2=[O:28])[CH:24]=[CH:23][C:22]=1[C:25]#[N:26]

Participants

5

Reactant 1

HCID 69027200HCID 69027200, compound

Product 1

HCID 17985220HCID 17985220, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(3-Amino-4-cyano-benzyl)-3-oxo-piperazine-1-carboxylic acid benzyl ester hydrochloride (4.0 g, 10.0 mmol) in CH3OH (45 ml) and CH2Cl2 (10 ml) is added 10% Pd on carbon (0.6 g). The mixture is stirred under an atmosphere of H2 for 2 hours then is filtered through a pad of celite. The filtrate is concentrated and the residue purified by column chromatography eluting with 10% 7M NH3 in CH3OH/CH2Cl2 to yield the title compound (1.62 g, 7.0 mmol). 1H NMR (DMSO, 300 MHz) δ7.34 (d, 1H), 6.64 (s, 1H), 6.46 (d, 1H), 6.04 (bs, 2H), 4.40 (s, 2H), 3.28 (s, 2H), 3.14 (m, 2H), 2.87 (m, 2H), 2.77 (bs, 1H). MS (ion spray): m/z 231 (M+H)+.

Workup

  1. filtrationthen is filtered through a pad of celite
  2. concentrationThe filtrate is concentrated
  3. customthe residue purified by column chromatography
  4. washeluting with 10% 7M NH3 in CH3OH/CH2Cl2

Sources & evidence

ORD record
ord-5b2f3ddf90e34a8aa0c46ae1f8e14f20
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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